Protected Sphingosine from Phytosphingosine as an
Efficient Acceptor in Glycosylation Reaction
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Abstract
A convenient, simple, and high-yielding
five-step synthesis of
a sphingosine acceptor from phytosphingosine is reported, and its
behavior in glycosylation reactions is described. Different synthetic
paths to sphingosine acceptors using tetrachlorophthalimide as a protecting
group for the sphingosine amino function and different glycosylation
methods have been explored. Among the acceptors tested, the easiest
accessible acceptor, unprotected on the two hydroxyl groups in positions
1 and 3, was regioselectively glycosylated on the primary position,
the regioselectivity depending on the donor used